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Potassium Carbonate → 5-bromo-1-{[1-(2-fluorobenzyl)-4-hydroxypiperidin-4-yl]-methyl}-pyridin-2(1H)-one

HRID 1410555
Notes
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Reaction equation

HRID 1410555 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4][N:5]1[CH2:12][CH2:11][C:8]2([O:10][CH2:9]2)[CH2:7][CH2:6]1.[Br:17][C:18]1[CH:19]=[CH:20][C:21]([OH:24])=[N:22][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].Cl.CCO>C(O)C.C(OCC)(=O)C.CN(C)C=O>[Br:17][C:18]1[CH:19]=[CH:20][C:21](=[O:24])[N:22]([CH2:9][C:8]2([OH:10])[CH2:11][CH2:12][N:5]([CH2:4][C:3]3[CH:13]=[CH:14][CH:15]=[CH:16][C:2]=3[F:1])[CH2:6][CH2:7]2)[CH:23]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 21887872Ethanol hydrochlorideHCID 86695293HCID 86695293, compoundHCID 178515818HCID 178515818, compound

Product 1

HCID 866952965-bromo-1-{[1-(2-fluorobenzyl)-4-hydroxypiperidin-4-yl]-methyl}-pyridin-2(1H)-oneYield 69.3%

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 21584252Ethanol ethylacetateSolvent

Procedure

7.00 g (0.0316 mol) of N-(2-fluorobenzyl)-1-oxa-6-azaspiro[2,5]-octane and 5.50 g (0.0314 mol) of 5-bromo-2-hydroxy-pyridine were weighed and added into 40 mL of N,N-dimethylformamide, and then 0.53 g (0.004 mol) of potassium carbonate was added. The reaction was stirred and reacted at a bath temperature of about 80° C. for 1 day and the solvent was recovered under reduced pressure. Potassium carbonate aqueous solution was added to the residue and the mixture was extracted with dichloromethane twice, combined, washed with water and dried, and the solvent was recovered. The residue was crystallized with petroleum ether-ethyl acetate to obtain a colorless flake-like crystal, 4.20 g, yield 69.3%. 1H-NMR (CDCl3, ppm) δ: 7.413 (1H, s), 7.399 (1H, dd, J1=8.20 Hz, J2=2.80 Hz), 7.358 (1H, t×d, J1=7.28 Hz, J2=1.68 Hz), 7.229 (1H, m), 7.096 (1H, t×d, J1=7.56 Hz, J2=1.12 Hz), 7.021 (1H, hept→t, J1=9.80 Hz), 6.543 (1H, dd, J=8.12 Hz), 3.994 (2H, s), 3.848 (1H, s), 3.602 (2H, s), 2.699 (2H, dd, J1=7.56 Hz, J2=3.82 Hz), 2.46 (2H, t×d, J1=8.96 Hz, J2=2.52 Hz), 1.54-1.74 (4H, m). The product was heated and dissolved in ethanol-ethyl acetate, salified with HCl-EtOH while warm and naturally cooled to obtain a colorless fine granular crystal, which was dried under vacuum to obtain 4.60 g product. Melting point: 184-186° C.

Workup

  1. customreacted at a bath temperature of about 80° C. for 1 day
  2. customthe solvent was recovered under reduced pressure
  3. additionPotassium carbonate aqueous solution was added to the residue
  4. extractionthe mixture was extracted with dichloromethane twice
  5. washwashed with water
  6. customdried
  7. customthe solvent was recovered
  8. customThe residue was crystallized with petroleum ether-ethyl acetate
  9. customto obtain a colorless flake-like crystal, 4.20 g, yield 69.3%
  10. temperatureThe product was heated
  11. temperaturewhile warm
  12. temperaturenaturally cooled
  13. customto obtain a colorless fine granular crystal, which
  14. customwas dried under vacuum

Sources & evidence

ORD record
ord-7ef2144cafcd443891ba65349fb409ba
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08921563B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes